NPASS Compound

Structure

NPC4299 OpenBabel07101719152D 26 25 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 22 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.28
Volume:	413.683
LogP:	3.601
LogD:	3.441
LogS:	-4.021
# Rotatable Bonds:	14
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	3.904
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.536
MDCK Permeability:	2.822509668476414e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.202
Human Intestinal Absorption (HIA):	0.206
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.098

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937
Plasma Protein Binding (PPB):	86.02689361572266%
Volume Distribution (VD):	0.875
Pgp-substrate:	8.931313514709473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	7.27
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.867
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.951
Carcinogencity:	0.353
Eye Corrosion:	0.007
Eye Irritation:	0.308
Respiratory Toxicity:	0.02

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC4299

Natural Product ID:	NPC4299
*Common Name:**	(2E,6Z,11S,12R)-3,7,11,15-Tetramethylhexadeca-2,6,14-Trien-7-[(Acetyloxy)Methyl]-1,12,19-Triol
IUPAC Name:	[(2Z,6S,7R)-7-hydroxy-2-[(E)-6-hydroxy-4-methylhex-4-enylidene]-6,10-dimethylundec-9-enyl] acetate
Synonyms:
Standard InCHIKey:	JZVYLXIIJTXKCL-CSQYNZLRSA-N
Standard InCHI:	InChI=1S/C22H38O4/c1-17(2)12-13-22(25)19(4)9-7-11-21(16-26-20(5)24)10-6-8-18(3)14-15-23/h10,12,14,19,22-23,25H,6-9,11,13,15-16H2,1-5H3/b18-14+,21-10-/t19-,22+/m0/s1
SMILES:	CC(=CC[C@H]([C@@H](C)CCC/C(=C/CC/C(=C/CO)/C)/COC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227193
PubChem CID:	16681370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001357] Acyclic diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29090	Carpesium triste	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[17432904]
NPO29090	Carpesium triste	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[556027]
NPT27	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[556027]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC4299 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1252
0.2-0.3	5247
0.3-0.4	15507
0.4-0.5	10662
0.5-0.6	6111
0.6-0.7	3031
0.7-0.8	662
0.8-0.85	40
0.85-0.9	9
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC101622
0.9412	High Similarity	NPC477085
0.9265	High Similarity	NPC477086
0.9265	High Similarity	NPC477087
0.9265	High Similarity	NPC472254
0.9155	High Similarity	NPC84360
0.8841	High Similarity	NPC329904
0.8841	High Similarity	NPC473361
0.875	High Similarity	NPC469880
0.8667	High Similarity	NPC112868
0.8649	High Similarity	NPC471537
0.8649	High Similarity	NPC86971
0.8649	High Similarity	NPC477088
0.8462	Intermediate Similarity	NPC122239
0.8451	Intermediate Similarity	NPC477084
0.8421	Intermediate Similarity	NPC474894
0.8421	Intermediate Similarity	NPC315731
0.8421	Intermediate Similarity	NPC475944
0.8406	Intermediate Similarity	NPC472266
0.84	Intermediate Similarity	NPC139712
0.8378	Intermediate Similarity	NPC315394
0.8378	Intermediate Similarity	NPC40049
0.8378	Intermediate Similarity	NPC476439
0.831	Intermediate Similarity	NPC469660
0.8267	Intermediate Similarity	NPC474816
0.8267	Intermediate Similarity	NPC209135
0.8243	Intermediate Similarity	NPC477202
0.8228	Intermediate Similarity	NPC471494
0.8205	Intermediate Similarity	NPC474809
0.8205	Intermediate Similarity	NPC23748
0.8194	Intermediate Similarity	NPC316185
0.8182	Intermediate Similarity	NPC184208
0.8182	Intermediate Similarity	NPC8538
0.8169	Intermediate Similarity	NPC269841
0.8169	Intermediate Similarity	NPC151481
0.8158	Intermediate Similarity	NPC242767
0.8158	Intermediate Similarity	NPC325869
0.8133	Intermediate Similarity	NPC477203
0.8133	Intermediate Similarity	NPC7563
0.8133	Intermediate Similarity	NPC320630
0.8133	Intermediate Similarity	NPC116177
0.8133	Intermediate Similarity	NPC262747
0.8125	Intermediate Similarity	NPC311163
0.8101	Intermediate Similarity	NPC474776
0.8101	Intermediate Similarity	NPC160517
0.8101	Intermediate Similarity	NPC78673
0.8101	Intermediate Similarity	NPC186155
0.8077	Intermediate Similarity	NPC471298
0.803	Intermediate Similarity	NPC226848
0.8028	Intermediate Similarity	NPC305698
0.8026	Intermediate Similarity	NPC93763
0.8026	Intermediate Similarity	NPC108816
0.8025	Intermediate Similarity	NPC313658
0.8025	Intermediate Similarity	NPC316138
0.8	Intermediate Similarity	NPC11804
0.8	Intermediate Similarity	NPC96663
0.8	Intermediate Similarity	NPC35933
0.8	Intermediate Similarity	NPC301525
0.8	Intermediate Similarity	NPC271070
0.8	Intermediate Similarity	NPC255307
0.7975	Intermediate Similarity	NPC49208
0.7975	Intermediate Similarity	NPC472473
0.7975	Intermediate Similarity	NPC161045
0.7975	Intermediate Similarity	NPC471297
0.7973	Intermediate Similarity	NPC315843
0.7949	Intermediate Similarity	NPC52861
0.7941	Intermediate Similarity	NPC55376
0.7922	Intermediate Similarity	NPC89128
0.7922	Intermediate Similarity	NPC226226
0.7922	Intermediate Similarity	NPC55304
0.7901	Intermediate Similarity	NPC475461
0.7901	Intermediate Similarity	NPC61527
0.7901	Intermediate Similarity	NPC305475
0.7901	Intermediate Similarity	NPC116575
0.7887	Intermediate Similarity	NPC473357
0.7887	Intermediate Similarity	NPC259299
0.7887	Intermediate Similarity	NPC193029
0.7875	Intermediate Similarity	NPC70424
0.7875	Intermediate Similarity	NPC114979
0.7875	Intermediate Similarity	NPC141193
0.7875	Intermediate Similarity	NPC96259
0.7875	Intermediate Similarity	NPC243618
0.7875	Intermediate Similarity	NPC191476
0.7875	Intermediate Similarity	NPC476804
0.7857	Intermediate Similarity	NPC282760
0.7848	Intermediate Similarity	NPC89555
0.7848	Intermediate Similarity	NPC323251
0.7838	Intermediate Similarity	NPC329890
0.7826	Intermediate Similarity	NPC29697
0.7805	Intermediate Similarity	NPC199382
0.7805	Intermediate Similarity	NPC474765
0.7792	Intermediate Similarity	NPC267231
0.7792	Intermediate Similarity	NPC127526
0.7792	Intermediate Similarity	NPC196653
0.7792	Intermediate Similarity	NPC471465
0.7778	Intermediate Similarity	NPC137033
0.7778	Intermediate Similarity	NPC165162
0.7778	Intermediate Similarity	NPC261380
0.7763	Intermediate Similarity	NPC256720
0.7763	Intermediate Similarity	NPC236228
0.7763	Intermediate Similarity	NPC476317
0.7763	Intermediate Similarity	NPC279537
0.7763	Intermediate Similarity	NPC61863
0.775	Intermediate Similarity	NPC472377
0.775	Intermediate Similarity	NPC44261
0.775	Intermediate Similarity	NPC131669
0.775	Intermediate Similarity	NPC16488
0.775	Intermediate Similarity	NPC40746
0.775	Intermediate Similarity	NPC231601
0.775	Intermediate Similarity	NPC169575
0.775	Intermediate Similarity	NPC311070
0.775	Intermediate Similarity	NPC473390
0.775	Intermediate Similarity	NPC42476
0.7738	Intermediate Similarity	NPC476004
0.7738	Intermediate Similarity	NPC3952
0.7738	Intermediate Similarity	NPC474761
0.7738	Intermediate Similarity	NPC78973
0.7733	Intermediate Similarity	NPC107654
0.7733	Intermediate Similarity	NPC474280
0.7733	Intermediate Similarity	NPC471525
0.7733	Intermediate Similarity	NPC140287
0.7733	Intermediate Similarity	NPC470686
0.7722	Intermediate Similarity	NPC24417
0.7722	Intermediate Similarity	NPC325031
0.7714	Intermediate Similarity	NPC34883
0.7711	Intermediate Similarity	NPC474471
0.7711	Intermediate Similarity	NPC227379
0.7711	Intermediate Similarity	NPC472378
0.7692	Intermediate Similarity	NPC470239
0.7692	Intermediate Similarity	NPC470244
0.7692	Intermediate Similarity	NPC321728
0.7683	Intermediate Similarity	NPC261721
0.7683	Intermediate Similarity	NPC315395
0.7683	Intermediate Similarity	NPC329692
0.7683	Intermediate Similarity	NPC316426
0.7683	Intermediate Similarity	NPC47220
0.7683	Intermediate Similarity	NPC186332
0.7681	Intermediate Similarity	NPC271282
0.7681	Intermediate Similarity	NPC325929
0.7681	Intermediate Similarity	NPC66460
0.7671	Intermediate Similarity	NPC475004
0.7671	Intermediate Similarity	NPC239373
0.7671	Intermediate Similarity	NPC329989
0.7662	Intermediate Similarity	NPC474278
0.7654	Intermediate Similarity	NPC102048
0.7654	Intermediate Similarity	NPC158756
0.7654	Intermediate Similarity	NPC126518
0.7654	Intermediate Similarity	NPC471301
0.7654	Intermediate Similarity	NPC474865
0.7654	Intermediate Similarity	NPC31086
0.7654	Intermediate Similarity	NPC82297
0.7654	Intermediate Similarity	NPC9868
0.7654	Intermediate Similarity	NPC471302
0.7647	Intermediate Similarity	NPC475931
0.7639	Intermediate Similarity	NPC73603
0.7632	Intermediate Similarity	NPC113639
0.7632	Intermediate Similarity	NPC329852
0.7632	Intermediate Similarity	NPC199445
0.7625	Intermediate Similarity	NPC85772
0.7625	Intermediate Similarity	NPC474252
0.7625	Intermediate Similarity	NPC229825
0.7625	Intermediate Similarity	NPC474291
0.7619	Intermediate Similarity	NPC474032
0.7619	Intermediate Similarity	NPC295312
0.7619	Intermediate Similarity	NPC20946
0.7619	Intermediate Similarity	NPC212598
0.7619	Intermediate Similarity	NPC246028
0.7619	Intermediate Similarity	NPC133450
0.7606	Intermediate Similarity	NPC308844
0.76	Intermediate Similarity	NPC16349
0.76	Intermediate Similarity	NPC327383
0.76	Intermediate Similarity	NPC185186
0.76	Intermediate Similarity	NPC222244
0.76	Intermediate Similarity	NPC329914
0.7595	Intermediate Similarity	NPC472470
0.7595	Intermediate Similarity	NPC474739
0.759	Intermediate Similarity	NPC312561
0.759	Intermediate Similarity	NPC471055
0.759	Intermediate Similarity	NPC477959
0.759	Intermediate Similarity	NPC86005
0.759	Intermediate Similarity	NPC166857
0.759	Intermediate Similarity	NPC131329
0.759	Intermediate Similarity	NPC471056
0.7571	Intermediate Similarity	NPC473508
0.7571	Intermediate Similarity	NPC217940
0.7568	Intermediate Similarity	NPC64234
0.7568	Intermediate Similarity	NPC316029
0.7568	Intermediate Similarity	NPC129630
0.7568	Intermediate Similarity	NPC476037
0.7568	Intermediate Similarity	NPC37929
0.7564	Intermediate Similarity	NPC260814
0.7564	Intermediate Similarity	NPC323249
0.7564	Intermediate Similarity	NPC39547
0.7564	Intermediate Similarity	NPC192006
0.7564	Intermediate Similarity	NPC474005
0.7564	Intermediate Similarity	NPC27949
0.7561	Intermediate Similarity	NPC474369
0.7561	Intermediate Similarity	NPC163606
0.7561	Intermediate Similarity	NPC21469
0.7561	Intermediate Similarity	NPC67081

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC4299 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1749
0.2-0.3	3769
0.3-0.4	2397
0.4-0.5	804
0.5-0.6	214
0.6-0.7	58
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7975	Intermediate Similarity	NPD7154	Phase 3
0.7857	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5362	Discontinued
0.7654	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4819	Approved
0.7595	Intermediate Similarity	NPD4822	Approved
0.7595	Intermediate Similarity	NPD4821	Approved
0.7595	Intermediate Similarity	NPD4820	Approved
0.7564	Intermediate Similarity	NPD4268	Approved
0.7564	Intermediate Similarity	NPD4271	Approved
0.7531	Intermediate Similarity	NPD5332	Approved
0.7531	Intermediate Similarity	NPD5331	Approved
0.7529	Intermediate Similarity	NPD46	Approved
0.7529	Intermediate Similarity	NPD7838	Discovery
0.7529	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD4790	Discontinued
0.7407	Intermediate Similarity	NPD4269	Approved
0.7407	Intermediate Similarity	NPD4270	Approved
0.7342	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5785	Approved
0.7262	Intermediate Similarity	NPD5786	Approved
0.7241	Intermediate Similarity	NPD7983	Approved
0.7176	Intermediate Similarity	NPD4251	Approved
0.7176	Intermediate Similarity	NPD4250	Approved
0.716	Intermediate Similarity	NPD4252	Approved
0.7159	Intermediate Similarity	NPD5779	Approved
0.7159	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5363	Approved
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD4249	Approved
0.7045	Intermediate Similarity	NPD7637	Suspended
0.7042	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5344	Discontinued
0.6988	Remote Similarity	NPD6435	Approved
0.6986	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD8039	Approved
0.6957	Remote Similarity	NPD4225	Approved
0.6944	Remote Similarity	NPD368	Approved
0.6923	Remote Similarity	NPD7839	Suspended
0.6923	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7639	Approved
0.6882	Remote Similarity	NPD7640	Approved
0.6818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6101	Approved
0.6818	Remote Similarity	NPD5370	Suspended
0.6812	Remote Similarity	NPD342	Phase 1
0.6774	Remote Similarity	NPD7638	Approved
0.675	Remote Similarity	NPD8264	Approved
0.6747	Remote Similarity	NPD5368	Approved
0.6716	Remote Similarity	NPD6927	Phase 3
0.6711	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6695	Phase 3
0.6702	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.663	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6051	Approved
0.6628	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5209	Approved
0.6533	Remote Similarity	NPD3197	Phase 1
0.6506	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6422	Discontinued
0.6462	Remote Similarity	NPD4265	Approved
0.6436	Remote Similarity	NPD6371	Approved
0.6429	Remote Similarity	NPD6929	Approved
0.642	Remote Similarity	NPD6924	Approved
0.642	Remote Similarity	NPD6926	Approved
0.6413	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD7750	Discontinued
0.6404	Remote Similarity	NPD7524	Approved
0.6386	Remote Similarity	NPD5776	Phase 2
0.6386	Remote Similarity	NPD4756	Discovery
0.6386	Remote Similarity	NPD6925	Approved
0.6373	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6930	Phase 2
0.6353	Remote Similarity	NPD7514	Phase 3
0.6353	Remote Similarity	NPD7332	Phase 2
0.6353	Remote Similarity	NPD6931	Approved
0.6329	Remote Similarity	NPD6923	Approved
0.6329	Remote Similarity	NPD6922	Approved
0.631	Remote Similarity	NPD7145	Approved
0.63	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6902	Approved
0.6267	Remote Similarity	NPD4194	Approved
0.6267	Remote Similarity	NPD4193	Approved
0.6267	Remote Similarity	NPD4191	Approved
0.6267	Remote Similarity	NPD4192	Approved
0.6265	Remote Similarity	NPD6933	Approved
0.625	Remote Similarity	NPD7143	Approved
0.625	Remote Similarity	NPD7144	Approved
0.6238	Remote Similarity	NPD6686	Approved
0.6224	Remote Similarity	NPD7632	Discontinued
0.6197	Remote Similarity	NPD3194	Approved
0.6197	Remote Similarity	NPD3196	Approved
0.6197	Remote Similarity	NPD3195	Phase 2
0.6197	Remote Similarity	NPD4266	Approved
0.618	Remote Similarity	NPD1694	Approved
0.6173	Remote Similarity	NPD7152	Approved
0.6173	Remote Similarity	NPD7150	Approved
0.6173	Remote Similarity	NPD7151	Approved
0.617	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD6647	Phase 2
0.6154	Remote Similarity	NPD7331	Phase 2
0.6154	Remote Similarity	NPD6053	Discontinued
0.6145	Remote Similarity	NPD7339	Approved
0.6145	Remote Similarity	NPD6942	Approved
0.6136	Remote Similarity	NPD6110	Phase 1
0.6129	Remote Similarity	NPD7087	Discontinued
0.6129	Remote Similarity	NPD7515	Phase 2
0.6098	Remote Similarity	NPD4732	Discontinued
0.6092	Remote Similarity	NPD6898	Phase 1
0.6087	Remote Similarity	NPD1695	Approved
0.6081	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD6109	Phase 1
0.6075	Remote Similarity	NPD7505	Discontinued
0.6075	Remote Similarity	NPD7115	Discovery
0.6071	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4786	Approved
0.6056	Remote Similarity	NPD3172	Approved
0.6047	Remote Similarity	NPD7645	Phase 2
0.6027	Remote Similarity	NPD4219	Approved
0.6023	Remote Similarity	NPD3667	Approved
0.6019	Remote Similarity	NPD6413	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD6932	Approved
0.5979	Remote Similarity	NPD7902	Approved
0.5979	Remote Similarity	NPD6083	Phase 2
0.5979	Remote Similarity	NPD6084	Phase 2
0.5977	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7525	Registered
0.5977	Remote Similarity	NPD7509	Discontinued
0.5972	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7146	Approved
0.5934	Remote Similarity	NPD7521	Approved
0.5934	Remote Similarity	NPD6409	Approved
0.5934	Remote Similarity	NPD6684	Approved
0.5934	Remote Similarity	NPD5330	Approved
0.5934	Remote Similarity	NPD7334	Approved
0.593	Remote Similarity	NPD3732	Approved
0.5905	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6640	Phase 3
0.5882	Remote Similarity	NPD4211	Phase 1
0.587	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6683	Phase 2
0.5856	Remote Similarity	NPD8516	Approved
0.5856	Remote Similarity	NPD8517	Approved
0.5856	Remote Similarity	NPD8515	Approved
0.5856	Remote Similarity	NPD8513	Phase 3
0.5842	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD7341	Phase 2
0.581	Remote Similarity	NPD6420	Discontinued
0.5806	Remote Similarity	NPD5737	Approved
0.5806	Remote Similarity	NPD6672	Approved
0.5806	Remote Similarity	NPD6903	Approved
0.5806	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD5343	Approved
0.5789	Remote Similarity	NPD3198	Approved
0.5775	Remote Similarity	NPD29	Approved
0.5775	Remote Similarity	NPD28	Approved
0.5773	Remote Similarity	NPD5695	Phase 3
0.575	Remote Similarity	NPD3704	Approved
0.5735	Remote Similarity	NPD39	Approved
0.5728	Remote Similarity	NPD6402	Approved
0.5728	Remote Similarity	NPD6675	Approved
0.5728	Remote Similarity	NPD5739	Approved
0.5728	Remote Similarity	NPD7128	Approved
0.5727	Remote Similarity	NPD7328	Approved
0.5727	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD3173	Approved
0.5714	Remote Similarity	NPD4220	Pre-registration
0.5714	Remote Similarity	NPD3666	Approved
0.5714	Remote Similarity	NPD8033	Approved
0.5714	Remote Similarity	NPD4228	Discovery
0.5696	Remote Similarity	NPD7909	Approved
0.5684	Remote Similarity	NPD7136	Phase 2
0.5676	Remote Similarity	NPD7516	Approved
0.5673	Remote Similarity	NPD6685	Approved
0.567	Remote Similarity	NPD5282	Discontinued
0.567	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7900	Approved
0.566	Remote Similarity	NPD6421	Discontinued
0.5652	Remote Similarity	NPD8273	Phase 1
0.5652	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD1696	Phase 3
0.5625	Remote Similarity	NPD8035	Phase 2
0.5625	Remote Similarity	NPD8377	Approved
0.5625	Remote Similarity	NPD8034	Phase 2
0.5625	Remote Similarity	NPD5693	Phase 1
0.5625	Remote Similarity	NPD8294	Approved
0.5619	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD6899	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data